Wanted to see if anyone has any advice on when it would it be a good time to cold call the list.

My building is a one month minimum so it's fairly easy to fill with 3 separate tenants, usually elderly couples from Canada, NY tri-state area, and cold midwest states.

Cold belt states can go for higher cap rates but also can take longer to re-tenant versus the warm belt states that are growing at a very fast pace with the retirees migrating away from the cold belt states.Some cold belt states have some excellent areas with great pockets of growth but not as expansive as the warm belt states.Hope it helps some.

I will hold out a little longer without as much anxiety and do some foot work around town.

Our loamy, clay soil has a high-elasticity, which means it moves with shifting temperature and moisture levels.The soil under your home expands and contracts with shifts between hot and cold conditions and through dry and wet cycles — literally moving your entire home.Your home was designed to handle this, but over time or after a big weather event your home can move beyond its limitations — that’s when you get foundation problems."

We met at a local bar and I closed while having a cold one.  

Maybe do it during summer months when it isn't cold and kids aren't in school, etc. 

If you dont maintain a constant marketing strategy whether that is direct mail, cold calling. or any other form of marketing you will stunt your efforts drastically. 

With "good" leads getting more and more scarce, where do you find most of your leads (cold calling, direct mail, driving for dollars, SEO, PPC)?

Mail all of them and consider cold calling the ones that are absentee, tax delinquent or high equity as well.Finally, you can also go to the real estate meetups that are nearby those areas you are looking to buy.